AlleyBoost hosted Nir Eyal and Brian Cohen at Mercy Collegeon Tues. November 4, 2014. I’ll post Nir’s talk in a separate post later this week. You can read about his chat at StartupGrind here.

Brian Cohen, chairman of NY Angels and author of What Every Angel Investor Wants You to Know, spoke about everything from angels to Pinterest, his most famous investment to date.

Brian Cohen talking to an entrepreneur while subtly showing off his book.

Although Cohen didn’t spend the whole time talking about Pinterest, the reasons he initially liked the startup illustrated many of the points he made during the fireside chat.

Cohen was the first investor in Pinterest. He likes to get in early and give the first check. He’s aware it’s risky, but sometimes it works out really well – like Pinterest well. What helped Ben Silbermann, cofounder of Pinterest, even more is that Cohen really liked him. Cohen cares a lot about the person he gives his money to.

“I like to know ideas early,” Cohen said, adding that founder’s backstory adds to the allure of the pitch. “I want to know the person behind the idea. Who are you? Where did you come from? Why did you think of that? A lot of times I want to be the first check.”

He calls everyone he has invested in a friend or someone he’d like to be considered friends with. This is because often times, the person is even more important than the idea. Not just because Cohen values friendship.

The reason the person is important is because they have to know how to build the business, even if it’s not the idea they started with.

“75 percent of the time the company I invest in is not doing the same thing 1 or 2 years later,” Cohen said. This was the case with Pinterest. The site started as an iPhone app called Tote, a catalog for women’s accessories, which in itself was a good enough idea with a good enough team to get Cohen on board.

Pinterest customers told the founders they wanted a way to collect all the things they liked. Silbermann cared a lot about what his customers thought. Using their feedback, he gave the world a place to digitally pin, and a new interface called a board. It duplicated an action people do in the real world online and it did what the customers asked for, which are factors in its success.

Today, Pinterest is valued at $5 billion. Cohen said almost no company gets that kind of valuation, most are somewhere between $2 and $4 million, depending on the sector and the team (serial entrepreneurs are valued higher). When it comes to investing, while valuation is a piece of the decision, he said it isn’t everything. He also doesn’t care about traction but said it helps increase the valuation.

Pitching advice Cohen, who studied rhetoric as an undergrad, believes in the power of a great communicator when it comes to pitching. He also believes in the power of a Google or LinkedIn search – meaning know the investors’ background. When speaking, be clear, crisp, clean and definitive. This means don’t use qualifiers like “I hope” or “We’re trying.” If those are the only words you can use to describe your business, it could mean you are in a position of weakness, and Cohen said that is a bad time to look for money.

For those who would rather “bootstrap” than raise money from a VC or Angel, Cohen thinks that’s stupid. He said people who are self-funding probably couldn’t convince anyone to invest. He also advises raising money six months before you need to it.

Remember to talk about exits in your pitch and have a timeframe in mind. Cohen said the average exit takes 6 to 10 years. Exits are important to angel investors – it’s how they make money.

“The word ‘exit’ to me is like sex – that is at the end the ultimate prize,” Cohen said.